Day Trips from Florence to Siena

Siena and San Gimignano are two of the most stunning locations in Tuscany, but a driver is essential for visiting them in a single day. Discover both during this full-day private tour, which includes round-trip transportation offered from either Florence or Livorno Port. Travel through rolling hills, vineyards, and villas. Tours include a Tuscan lunch and wine tasting at a hand-picked estate.

We will spend an entire day crossing the most characteristic and beautiful part of the Tuscan countryside: the Chianti. Here we will visit small villages and admire unique landscapes ... without forgetting to taste some good wine!

Experience the best Tuscany has to offer in just one day, with a private tour taking in Pisa, Siena, Diborrato Waterfall, and a wine tasting of local Chianti wines. After being picked up from your accommodation in Florence, explore historic Pisa and get those all-important pictures with the famous Leaning Tower. Discover beautiful San Gimignano and Diborrato Waterfall, before arriving at Siena. Here, your private guide explains the local history and enjoy a tasting of Chianti wine in a traditional bar or restaurant.

Spend a day uncovering the charm of Siena, San Gimignano, and the Chianti region with a private tour from Florence. Enjoy an intimate experience exploring Siena's vibrant main square, the picturesque hilltop town of San Gimignano, and the historic town of Castellina in Chianti. Complete your adventure with a visit to a local winery for a taste of Chianti wines, including rosè and Supertuscan, and insight into how sangiovese grapes are cultivated.

Taste some of Tuscany's most renowned varietals on a full-day private Chianti wine tour from Florence. Visit the charming medieval towns of Montalcino, Montepulciano, and Greve, where historic castles and towers appear untouched by time. In each village, stop at wineries and wine bars to sample pours of Nobile, Brunello, and Chianti Classico wines and learn about the cultivation of these prized grapes.

Explore the best of Tuscany in a single day on this private tour from Florence. Travel along scenic countryside roads to reach iconic destinations, including Siena, Pisa, and the UNESCO-listed hilltop town of San Gimignano. See famous landmarks such as the Leaning Tower of Pisa and Piazza del Campo without the hassle of planning your route. Enjoy private transportation and accommodation pickup upon request for added comfort.

There are no direct transport links between Florence and San Gimignano, so the best way to explore this UNESCO-listed hilltop village is by private car. Embark on a deluxe visit during this half-day, group tour, and visit key landmarks like the Duomo, San Agostino Church, the Museum of Holy Relics, and the 13 towers of its skyline. Tours stop at a wine estate, where travelers can opt for a tasting.

Pair the beauty of San Gimignano, a UNESCO World Heritage Site, with the classic flavors of Italian cuisine on this private adventure. Discover the walled city, home to some of the world’s best ice cream at Gelateria Dondoli, then head to a country farmhouse. Choose whether to make pizza, lasagne, or fresh egg pasta, then prepare and enjoy your Italian lunch with local Chianti wine.

Experience the very best of Tuscany on an unforgettable full-day journey from Florence, visiting four of the region's most iconic destinations in one seamless itinerary. Marvel at the world-famous Leaning Tower of Pisa, wander through the medieval streets of San Gimignano, explore the historic charm of Siena, and travel through the rolling vineyards of the renowned Chianti countryside. Savor the authentic flavors of Tuscany with a light winery lunch featuring regional cheeses, cured meats, local wines, and traditional Cantuccini biscuits. Along the way, enjoy spectacular landscapes of vineyards, olive groves, and picturesque hilltop villages that have made Tuscany one of Italy's most beloved destinations. Perfect for first-time visitors and lovers of history, culture, food, and wine, this expertly planned day trip lets you experience Tuscany's most famous highlights without the hassle of planning transportation. Reserve your place today and create unforgettable memories.

Escape the city and experience the very best of Tuscany on a full-day journey through its most iconic destinations. Travel comfortably from Florence to discover the medieval charm of Siena, the famous towers of San Gimignano, the rolling vineyards of the Chianti countryside, and the world-renowned Leaning Tower of Pisa. Stroll through UNESCO World Heritage Sites, admire spectacular Renaissance and medieval architecture, taste authentic Tuscan wines and local specialties at a traditional winery, and capture unforgettable views of Tuscany's picturesque landscapes. Whether you're fascinated by history, passionate about Italian culture, or simply looking to experience Tuscany's timeless beauty, this tour offers the perfect combination of historic cities, scenic countryside, and authentic local flavors—all in one unforgettable day.

Explore the medieval town of San Gimignano before heading into the scenic Chianti hills on this private Tuscan experience, which includes lunch and wine tasting. Walk through cobblestone streets, enjoy a gelato or glass of Vernaccia, then travel to local wineries for a traditional Tuscan lunch and guided wine tastings. This tour blends cultural heritage with countryside charm and regional flavors for a well-rounded day in Tuscany with hotel pickup included.

Reaching Siena and San Gimignano from Florence by public transport requires separate connections to two different destinations—and coordinating a return journey from both in a single day takes planning that most visitors don't have time for. This full-day tour covers both UNESCO World Heritage-listed towns and offers free time in each to explore Piazza del Campo and San Gimignano's medieval towers independently.

Escape the crowds and experience the best of Tuscany with this private shore excursion from Livorno or Florence. Travel in comfort from your ship or hotel with a private driver and enjoy a small-group walking tour of San Gimignano, led by a local expert. Discover medieval towers, artisan shops, and breathtaking views in this UNESCO-listed town. Enhance your day with an optional wine tasting and Tuscan lunch at a renowned Super Tuscan winery, where you’ll sample Vernaccia di San Gimignano and other local labels in an authentic countryside setting. After lunch, continue to Siena, one of Tuscany’s most enchanting cities. Enjoy free time to explore Piazza del Campo, admire the Siena Cathedral from outside, and stroll the historic streets at your own pace. This flexible experience can be tailored to your cruise schedule, with guaranteed on-time return. Perfect for travelers seeking a mix of history, beauty, and flavor in a single day.

This tour ticks off two must-sees in Tuscany's collection, Siena and San Gimignano. You'll be picked up from your accommodation in Florence and taken for a full-day tour of these two cultural hotspots. You'll start with a walking tour of the old town of Siena. Siena Cathedral, one of Italy's most popular Romanesque-meets-Gothic churches is here, too, and you'll head inside it before heading into the city centre. In this part of Siena, the Piazza del Campo is the biggest draw. Shaped like a seashell, you'll find everything from a big water fountain to City Hall here. Then you'll hop back on your transport and make your way to San Gimignano, which is often known as the Manhattan of the Middle Ages because of its line-up of ancient towers. You'll head to a gelateria for a chance to try some ice-cream made by a master whose creations have won international championships. When you've had your fill and looked around San Gimignano, you'll be taken back to your accommodation in Florence.

This experience is suitable for everyone, even children. We will be in an open area admiring the wonderful Tuscan hills. We will stop at all the most scenic places to take beautiful photos.

This tour combines two of Tuscany’s most authentic medieval towns in a single day. In Volterra, you’ll enjoy a live alabaster carving demonstration in a traditional artisan workshop before exploring the historic center at your own pace. The experience continues in the perfectly preserved walled village of Monteriggioni, one of the most iconic sights in the Tuscan countryside.

we will make you experience Chianti as we do, in its beauty, goodness and simplicity, with fun and light-heartedness

Departure from your Accommodation or Hotel, travel in a van maximum 6 people , English speaking driver, each vehicle is equipped with fresh water. 1 stop city of Siena where you will have 1.5/2 hours to visit the city of the Palio, and those who love wine can visit the wine cellar in the tufa cave under the baptistery of Siena, with the possibility of wine tasting for a fee 2 stop town of San Gimignano where you will have 1 hour of time for Visiting and Shopping in the City of 7 Towers. stop at the local winery for tasting of local wines and visit of the company. Return to Florence where you were picked up, it is possible on your request to do a wine test and lunch in a winery in the San Gimignano area

Lilium Travel Florence offers a full-day, 9-hour journey through the heart of Tuscany with a private van tour (max 8 pax) from Florence. First, you’ll visit San Gimignano, the "Town of Towers," a stunning medieval gem and UNESCO World Heritage site. Explore its narrow streets, admire the well-preserved towers that once symbolized wealth and power, and soak in panoramic views of the surrounding Tuscan countryside. Next, head to the village of Monteriggioni, a perfectly preserved medieval fortress with its iconic walls and towers still standing proudly. Wander through the town, feeling as if you’ve stepped back in time. The final stop is Siena, famous for its unique medieval architecture and the breathtaking Piazza del Campo, home of the historic Palio horse race. Enjoy time to explore its cobbled streets, visit the stunning Siena Cathedral, and relax in one of its charming cafes. With ample free time at each location, this tour offers a perfect blend of history, culture, and relaxation.

Experience Tuscany’s highlights on a private day trip from Florence to Siena, San Gimignano, and Pisa. In Siena, explore the UNESCO-listed historic center, admire its Gothic cathedral, and visit the famous Piazza del Campo, home of the Palio horse race. Continue through the rolling hills to San Gimignano, the “Town of Towers,” where medieval skyscrapers, cobbled streets, and artisan shops await. Finish in Pisa, marveling at the iconic Leaning Tower and the stunning monuments of the Piazza dei Miracoli. With comfortable transport, a private guide, and flexible pacing, this exclusive Florence day tour offers a personalized way to see Tuscany’s most famous landmarks.

A wine tour in Chianti is an unforgettable experience for wine lovers and scenic beauty. This region, located between Florence and Siena, is famous all over the world for the production of Chianti Classico, a high quality red wine.

Sip wine and go back to medieval times during this small-group guided tour that includes an authentic Tuscan lunch. Wander the streets of the ancient, hilltop town of Montalcino known for its wine before touring the Brunello di Montalcino winery. Learn how biodynamic wines are made and sample varieties straight from the barrel. After lunch, visit a second winery to sip samples and eat Tuscan fare.

Immerse yourself in Italian wines on this small-group tour and experience the best of Florence and Chianti from a sidecar. Meet winemakers and visit a working winery to explore its production processes. Then, enjoy wine tastings and even a Tuscan lunch complete with local products. As you explore the vineyards on this sidecar adventure, snap great photos and videos of timeless countryside views.

Get a true taste of the Tuscan countryside with this day trip to Siena, San Gimignano, and a Chianti winery for dinner. Venture first to the city of Siena for a guided tour through the Piazza del Campo, as well as a surprise food tasting. Afterward, wander the hill town of San Gimignano before heading to a Chianti winery for a delicious dinner with fine local wine. Upgrade to include a visit to Pisa and Piazza dei Miracoli.